Process of manufacuring alkyl-ethers of morphin.



MAX C. TRAUB, OF BASE-L, SVJITZEBLAND.

DONALD MCKESSON. BOTH OF CHAPPAQUA. NEXV HAM. GEQRGE C. MGKESSON.HERBERT OF NEW YORK N. Y., COPABTNEBS QOMY OF NEW YORK, N. Y.

ASSIGNOP. TO JQHN MCKESSON. JR.. AND YORK. AND WILLIAM HULL "VVICK- D.ROBBINS. AND IRVING IVIGKESSON, ALL USING THE FIRM C-F WICKESSON &ROBBINS,

PROCESS OF INIANUFACURING ALKYLETHERS OF MORPHIN..

1,1oo,oos.

No Drawing.

To a uhom it may comm-n Be it known thatl. hlAX THAUB, a sub jcct. ofthe King of llavnria. residing: at-l Ba el, smvii'lzerland have inventedcertain new and useful improvements in Processes l of Manufacturing.\.ll(yl.lthers of Morphin, of which the following is a s 'iecitication.

My invention relates to a process for prcparing allcvl others ofinorphin and the ohjcct is to provide an economical method of preparingthe same. I

This process is hosed on the fact that morphin forms compounds withorganic alky :nninonium hoses in solution in a suitable solvent such asalcohol. ns it does with s0 diuin. potassium or other bases and thatfrom these compounds under certain condii tious alliyl others ol morphincauheohtaincd. The following description of the process relates to themethyl ether of rnorplnn as a i type, but. any other alkyl other ofmorphin can be produced by this process by nsingthe l desired organicalliyl annnoniuni hydroxid. l

The process for making the methyl ether of morphin consists indissolving the molec- Specification of Letters Patent.

Application filed May 6. 1912.

Patented June 23, 1914.

Seria1No,G95,398.

nlar quantity of a morphiu in an alcoholic olution of the (.csircdorganic allryl ammonium hydroxid. such trimethylphenyl annnonnnnlrvdrczid. methyl p vridin ammonium hydroxid, C ll NtC-ll lOH,tetraniethvl-anunoninm hydroxid, or other bases of this type. andheating this mixture for several hours on a water lit th in a refluxapparatus or in an anto 'lnv. The liquid is allowed tov cool and thelnorphin methyl other is separated, according to known methods, from themorphin thatlnight have escaped the reaction. For inrl'illltQ. ldissolve 1.5.2 parts by Weight of lriinethyl phcnyl ammoniumhydroxid in(500 parts of alcohol or some other suitable solvent. In this solution Idissolve 301 parts of inorphin and heat. the mixture on e. .natcr lmthin an autoclave or in an apparatns with rctlux' condenser for severalhours. \fter this time. the reaction is complete and. the products maybe isolated and purified. The chemical reaction is explained by theformula:

Trimethylpln-nyl Trhnethylphenyl ammonium ommoninm hydroxid. Morphin.morphhn \Vater. Diniethylanilin Codcin. CgngN a ennwnmon C llsN 4- H 0 CH N-CE CuHmNOn'KJIh CH 11; 011 CUHiB xO I claim as my invention I 1. Inthe process of preparing ulliyl others i of morphin, t-hcstep whichcomprises efr footing a reactionv between morphin and an organic nlliylammonium base. 52 In the process of. preparing allcvl others 0?n'iorphiin the step which comprises dissolution of annnonium hydroxid.

3. The process of preparing alli'yl others of morphin, which comprisesthe dissolving of morphin in e solution of an organic allryl solvingmorphin in a 1 l 1 l ammonium hydroxid anu heating the solul tion'. 1

4. The process of preparing alkyl ethersof morphin which consists indissolvingmoi phin in a solution of alkyl phenyl arnntionium hydroxidand boiling the solution for several hours.

5. 'lhe process of preparing the methyl:

I ethers of morpliin droxid in a suitable ganic ulliyl solving trimethylwhich consists in dissolving morphin in a. solution formed by dissolvingtrimetnyl phenyl ammonium hydroxid in :1 suitable solvent. and heating6. The. process of preparing the. methyl others of morphin whichconsists in dissolving' morphin in a. solution formed by dissolvingtrimet-hyl ph'enyl ammonium hysolvent and heating the solution forsever-oi hours.

7. The process of in airing the methyl others of morphin which comprisesdissolving the molecular quantity of morphin in an oramn'ioniumhydroxicl and heating the solution for several hours.

8. The process ofinaking the methyl others of morpliin which comprisesthe disvv ing of niorphin in asolution formed by disphenyl ammoniumby issolvent and heating.

droxid in a suite 9. The process of preparing the methyl others ofmorphin which comprises the dissolving of morphin in a solution formedby dissolving trimethyl phenyl ammonium hythis 14th day of March, A. D.,1912.

MAX C. TRAUB. Signerl in the presence of- GEO. Gwrom), ARNOLD ZUBER.

6 droxid in a solvent and heating the solution for several hours.

This specification signed and witnessed

